methyl (E)-3-[[(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methoxy]prop-2-enoate | 928780-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: methyl (E)-3-[[(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methoxy]prop-2-enoate
• CAS: 928780-08-9
• 化学式: C₁₆H₃₀O₅Si
• 分子量: 330.497
• InChiKey: PLZKIIULZQORTM-LLVNNSLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.26
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (E)-3-[[(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methoxy]prop-2-enoate 在 palladium on activated charcoal 氢气 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 3-[[(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methoxy]propan-1-ol
  参考文献：
  名称：

  Synthesis and antiproliferative activity of (2R,3R)-disubstituted tetrahydropyrans. Part 2: Effect of side chain homologation

  摘要：

  In this study, we synthesized a series of enantiomerically pure (2R,3R)- and (2R, 3 S)-disubstituted tetrahydropyrans bearing a CH2O spacer group on the side chain at position 2 of the heterocyclic ring. The in vitro antiproliferative activities of the compounds were examined in the human solid tumor cell lines A2780 (ovarian cancer), SW1573 (non-small cell lung cancer), and WiDr (colon cancer). Overall, the results point out the relevance for anti proliferative activity of the distance between the heterocycle and the unsaturated group. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.066
• 作为产物：
  描述：

  (2R,3R)-2-(hydroxymethyl)tetrahydro-2H-pyran-3-ol 在 咪唑 、 三丁基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 生成 methyl (E)-3-[[(2R,3R)-3-[tert-butyl(dimethyl)silyl]oxyoxan-2-yl]methoxy]prop-2-enoate
  参考文献：
  名称：

  Synthesis and antiproliferative activity of (2R,3R)-disubstituted tetrahydropyrans. Part 2: Effect of side chain homologation

  摘要：

  In this study, we synthesized a series of enantiomerically pure (2R,3R)- and (2R, 3 S)-disubstituted tetrahydropyrans bearing a CH2O spacer group on the side chain at position 2 of the heterocyclic ring. The in vitro antiproliferative activities of the compounds were examined in the human solid tumor cell lines A2780 (ovarian cancer), SW1573 (non-small cell lung cancer), and WiDr (colon cancer). Overall, the results point out the relevance for anti proliferative activity of the distance between the heterocycle and the unsaturated group. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.10.066